Optically active 1-(fluoro-, trifluoromethyl- or trifluoromethoxy- substituted phenyl)alkylamine N-monoalkyl derivatives and process for producing same

Abstract

An optically active 1-(fluoro-, trifluoromethyl- or trifluoromethoxy-substituted phenyl)alkylamine N-monoalkyl derivative represented by the formula 4 is produced by a process including (a) reacting an optically active secondary amine, represented by the formula 1, with an alkylation agent R 2 —X, in the presence of a base, thereby converting the secondary amine into an optically active tertiary amine represented by the formula 3; and (b) subjecting the tertiary amine to a hydrogenolysis, thereby producing the N-monoalkyl derivative, wherein R represents a fluorine atom, trifluoromethyl group or trifluoromethoxy group, n represents an integer of from 1 to 5, each of R 1 and R 2 independently represents an alkyl group having a carbon atom number of from 1 to 6, Me represents a methyl group, Ar represents a phenyl group or 1- or 2-naphthyl group, * represents a chiral carbon, and X represents a leaving group.

1. An optically active tertiary amine represented by the formula 3, 
       
         
           
           
               
               
           
         
       
       wherein
 R represents a fluorine atom, trifluoromethyl group or trifluoromethoxy group, 
 n represents an integer of from 1 to 5, 
 each of R 1  and R 2  independently represents an alkyl group having a carbon atom number of from 1 to 6, 
 Me represents a methyl group, 
 Ar represents a phenyl group or 1- or 2-naphthyl group, and 
 * represents a chiral carbon. 
 
     
     
       2. An optically active tertiary amine according to  claim 1 , which is represented by the following formula, 
       
         
           
           
               
               
           
         
       
     
     
       3. An optically active tertiary amine according to  claim 1 , which is represented by the following formula, 
       
         
           
           
               
               
           
         
       
     
     
       4. An optically active tertiary amine according to  claim 1 , which is represented by the following formula, 
       
         
           
           
               
               
           
         
       
     
     
       5. An optically active tertiary amine according to  claim 1 , which is represented by the following formula, 
       
         
           
           
               
               
           
         
       
     
     
       6. An optically active tertiary amine according to  claim 1 , which is represented by the following formula, 
       
         
           
           
               
               
           
         
       
     
     
       7. An optically active tertiary amine according to  claim 1 , which is represented by the following formula, 
       
         
           
           
               
               
           
         
       
     
     
       8. An optically active tertiary amine according to  claim 1 , which is represented by the following formula, 
       
         
           
           
               
               
           
         
       
     
     
       9. An optically active tertiary amine according to  claim 1 , which is represented by the following formula, 
       
         
           
           
               
               
           
         
       
     
     
       10. An optically active tertiary amine according to  claim 1 , which is represented by the following formula, 
       
         
           
           
               
               
           
         
       
     
     
       11. An optically active tertiary amine according to  claim 1 , which is represented by the following formula, 
       
         
           
           
               
               
           
         
       
     
     
       12. An optically active tertiary amine according to  claim 1 , which is represented by the following formula, 
       
         
           
           
               
               
           
         
       
     
     
       13. An optically active tertiary amine according to  claim 1 , which is represented by the following formula,